Potassium Bicarbonate → HCID 23251301, compound

Participants

Reaction Steps

A solution of crude 3α-acetoxy-5α-pregn-1-en-20-one (4.0 g.) containing some 3α-acetoxy-2α-bromo-5α-pregnan-20-one, in dry methanol (120 ml.) was treated with potassium bicarbonate (4.5 g.), and the mixture was refluxed under nitrogen for 2 hours. The reaction mixture was concentrated in vacuo, then poured into water, and the product was extracted with methylene chloride. The extract was washed with water, dried (Na2SO4), and evaporated in vacuo. The residue (3.3 g.) was subjected to preparative layer chromatography. The more polar fraction, after crystallisation from methyl acetate, gave 3α-hydroxy-5α-pregn-1-en-20-one (780 mg), m.p. 150°-154°, [α]D + 28.9°. The less polar fraction after crystallisation from methyl acetate, gave 2α-bromo-3α-hydroxy-5α-pregnan-20-one (320 mg), m.p. 201°-204°, [α]D + 110.5°.

Provenance & Evidence